OSL Retail Services | Remote Senior Systems Administrator

4 weeks ago


mississauga, Canada OSL Retail Services Full time

It’s an exciting time to be at OSL Retail Services, working for a people focused company that’s at the top of its game. The momentum we’ve generated in recent years with our commitments to client customers, innovation, business results, and an entrepreneurial spirit has created energy, enthusiasm, and engagement among our employees that is pushing us to new heights. At OSL, our culture is our foundation. Passionate employees, great customer service and long-term relationships are all built upon that foundation. OSL was established in 2012 in Mississauga, Ontario, to provide clients with customized designed sales solutions in retail, direct sales, merchandising and customer acquisition.

About the role: 5 days in Mississauga office

The Senior Systems Administrator will be instrumental in managing OSL’s corporate infrastructure and cybersecurity. Your expertise will ensure the highest reliability and performance, supporting our commitment to delivering exceptional service to our clients and customers. This role involves working on complex projects, including evolving existing systems and implementing new technologies.

Manage Corporate network environment: Architect and deploy network infrastructure, manage firewalls, VPNs, network troubleshooting, managing network security
Creates and maintains system configuration, mapping, processes, and problem management documentation
Based on a mix of Linux and Windows
Continuously monitor the corporate environment, with close attention to capacity and performance
Contribute to the tactical planning and direction of IT infrastructure and overall improvement of all service deliveries
Build out production monitoring: design and deploy infrastructure monitoring for all services, including API endpoints and external web applications and services
Implement security controls: ensuring the environment is secure and following best practices
Implement operational controls and processes, ensuring the mechanisms, safety controls, fuse breakers, and due diligence are in place to introduce changes and react responsibly to planned or unplanned events

Strong engineering background with experience in automation, configuration management, scripting, and security best practices
Familiarity with Infrastructure as Code (IaC) principles, automated builds, monitoring, and scaling
Experience with system and application monitoring tools such as Nagios, Prometheus, Grafana, ELK, etc.
Proficiency in Windows and Linux systems administration, including scripting, troubleshooting, and upgrading
Ability to take ownership of technical delivery and collaborate effectively with business partners
It is crucial to assume leadership responsibilities for troubleshooting and managing incidents in the environment. This requires weighing desired outcomes against risk and urgency. This responsibility may also involve working with OSL's vast network of partner service providers.
Strong scripting and coding capabilities to integrate / instrument OSL’s technology stack.
Excellent communication and stakeholder management skills, with the ability to convey complex technical concepts to non-technical audiences.
5+ years of demonstrated experience in the field.
~ Strong knowledge of networking protocols and services (TCP/IP, DNS, DHCP, VPN, etc.).
~ Expert or near-expert skills with Windows, Linux, networking, storage, and containerization
~ Experience with server provisioning and configuration management, utilizing tools such as Terraform, Ansible or Chef, delivering Infrastructure as Code
~ Experience with database administration of MSSQL and PostgreSQL
~ Observability, monitoring and alerting with tools like Prometheus and Datadog


Training and development opportunities to grow your career with one of Canada’s Best Managed Companies
OSL is committed to an inclusive workplace that does not discriminate against race, nationality, religion, age, marital status, physical or mental disability, sexual orientation, gender, or gender identity. We believe in diversity and encourage any qualified individual to apply.



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  • Mississauga, Canada OSL Retail Services Full time

    It’s an exciting time to be at OSL Retail Services, working for a people focused company that’s at the top of its game. The momentum we’ve generated in recent years with our commitments to client customers, innovation, business results, and an entrepreneurial spirit has created energy, enthusiasm, and engagement among our employees that is pushing us...


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